Acetic Acid → [1-(3,5-Diisopropoxy-benzyl)-piperidin-4-yl]-carbamic acid tert-butyl ester

HRID 2242960

반응식

HRID 2242960 반응식
[C:1]([O:5][C:6](=[O:14])[NH:7][CH:8]1[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]1)([CH3:4])([CH3:3])[CH3:2].[CH:15]([O:18][C:19]1[CH:20]=[C:21]([CH:24]=[C:25]([O:27][CH:28]([CH3:30])[CH3:29])[CH:26]=1)[CH:22]=O)([CH3:17])[CH3:16].C(O)(=O)C.C([BH3-])#N.[Na+]>C(O)C>[C:1]([O:5][C:6](=[O:14])[NH:7][CH:8]1[CH2:13][CH2:12][N:11]([CH2:22][C:21]2[CH:24]=[C:25]([O:27][CH:28]([CH3:30])[CH3:29])[CH:26]=[C:19]([O:18][CH:15]([CH3:17])[CH3:16])[CH:20]=2)[CH2:10][CH2:9]1)([CH3:4])([CH3:2])[CH3:3]

참가 물질

6

반응물 4

HCID 176Acetic AcidHCID 7238334-(N-Boc-amino)piperidineHCID 5003444Sodium cyanoborohydrideHCID 113106053,5-diisopropoxybenzaldehyde2회

생성물 1

HCID 67147306[1-(3,5-Diisopropoxy-benzyl)-piperidin-4-yl]-carbamic acid tert-butyl ester

시약·촉매·용매 1

HCID 702Ethanol용매2회

반응 조건

온도
100 °C

실험 절차

A mixture of piperidin-4-yl-carbamic acid tert-butyl ester (4.0 g, 20.0 mmol, 1.0 equiv), 3,5-diisopropoxy-benzaldehyde (5.33 g, 24.0 mmol, 1.2 equiv; intermediate D7, vide infra) and acetic acid (4.6 mL, 4.80 g, 80.0 mmol, 4.0 equiv) in ethanol (16 mL) was heated by microwave irradiation to 100° C. for 5 min. Sodium cyanoborohydride (2.51 g, 40.0 mmol, 2.0 equiv), dissolved in ethanol (8 mL), was added and the reaction mixture heated by microwave irradiation to 100° C. for an additional time period of 10 min. The solvent was removed under reduced pressure and the crude reaction product extracted from a solution of 1 M NaOH (100 mL) with ethyl acetate (3×100 mL). The combined organic phases were dried over MgSO4, concentrated by evaporation under reduced pressure and the crude material purified on a Isolute flash NH2 chromatography column using a MPLC system (CombiFlash Companion, Isco Inc.) eluting with a gradient of heptane/ethyl acetate providing 3.23 g (40%) of the title compound. MS (ISP): 407.4 [M+H]+.

후처리

  1. additionwas added
  2. temperaturethe reaction mixture heated by microwave irradiation to 100° C. for an additional time period of 10 min
  3. customThe solvent was removed under reduced pressure
  4. customthe crude reaction product
  5. extractionextracted from a solution of 1 M NaOH (100 mL) with ethyl acetate (3×100 mL)
  6. dry with materialThe combined organic phases were dried over MgSO4
  7. concentrationconcentrated by evaporation under reduced pressure
  8. customthe crude material purified on a Isolute flash NH2 chromatography column
  9. washeluting with a gradient of heptane/ethyl acetate providing 3.23 g (40%) of the title compound

출처 및 근거

ORD 기록
ord-83e9396f01504c359dd69a736c788ad2
출처 데이터셋
uspto-grants-2010_03
특허 번호
US07674804B2

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